Jay Bregman

Jay Bregman is a serial entrepreneur and the founder and CEO of Thimble, an insurance company focused on providing flexible coverage for small businesses and independent workers.14

Professional Background

Bregman has over 20 years of experience as an entrepreneur.2 Prior to founding Thimble, he:

• Co-founded Hailo, a London-based ridesharing company that was later acquired by Daimler Mercedes-Benz in 20161
• Founded eCourier, a technology-enabled services company that was acquired by Royal Mail1

Education

Bregman holds:

• A Bachelor's degree from Dartmouth College, where he studied philosophy12
• A Master's degree from the London School of Economics and Political Science1

Thimble

As the CEO of Thimble, Bregman is leading the company to revolutionize the small business insurance market:

• Thimble offers on-demand insurance by the hour, day, or month1
• The company aims to cover the 57 million people who work independently1
• Thimble has raised over $29 million from investors including IAC1

Bregman's approach at Thimble is informed by his belief that "unsexy businesses are the best" and his philosophy of "think wild and act tame".1

Personal Insights

Bregman comes from a family of doctors but was encouraged to pursue inventing rather than medicine.1 He is known for his reflections on entrepreneurship and the lessons he's learned throughout his career, which he applies to his work at Thimble.3